Tetra-n-butyl­ammonium tetra­kis(penta­fluoro­phen­yl)borate

Schödel, F.; Lerner, H.-W.; Bru Roig, M.; Bolte, M.

doi:10.1107/S1600536805040134

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Tetra-n-butylammonium tetrakis(pentafluorophenyl)borate

F. Schödel, H.-W. Lerner, M. Bru Roig and M. Bolte

In the title compound, C₁₆H₃₆N⁺·C₂₄BF₂₀^-, the geometric parameters do not show any unusual values. The four n-butyl chains adopt an all-trans conformation.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805040134/at6058sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805040134/at6058Isup2.hkl Contains datablock I

CCDC reference: 296509

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.005 Å
R factor = 0.033
wR factor = 0.075
Data-to-parameter ratio = 6.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT431_ALERT_2_B Short Inter HL..A Contact  F54    ..  F66     ..       2.57 Ang.

Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       6.88
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.03 Ratio
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.61
           From the CIF: _reflns_number_total               3854
           Count of symmetry unique reflns         3898
           Completeness (_total/calc)             98.87%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion


checkCIF publication errors

Alert level A
PUBL006_ALERT_1_A  _publ_requested_journal is missing
            e.g. 'Acta Crystallographica Section C'

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

Comment top

Very strong cationic Lewis acids are only available in the presence of weakly coordinating counter-ions such as [B(C₆F₅)₄]⁻. These anions also play an important role in electrochemistry. The salt [nBu₄N]⁺·[B(C₆F₅)₄]⁻ possesses a low reactivity towards reducing and oxidizing agents. Moreover, conductance measurements show that the dissociation constant of [nBu₄N]⁺·[B(C₆F₅)₄]⁻ solutions in solvents with low polarity are greater than those of smaller traditional anions (LeSuer et al., 2004). Therefore, we are convinced that tetra-n-butylammonium tetrakis(pentafluorophenyl)borate, (I), is an ideal supporting electrolyte. According to a literature procedure (LeSuer et al., 2004), we have synthesized (I) and we report here the crystal structure.

Perspective views of the cation and anion of (I) are shown in Figs. 1 and 2, respectively. Bond lengths and angles can be regarded as normal (Cambridge Crystallographic Database; Version 1.6 plus three updates; Mogul Version 1.0; Allen, 2002). Compound (I) consists of discrete tetrakis(pentafluorophenyl)borate anions and tetra-nbutylammonium cations. The four n-butyl chains adopt an all-trans conformation.

Experimental top

Compound (I) was synthesized according to a literature procedure. Colourless crystals of the title compound suitable for X-ray diffraction were grown from a methanol solution at 253 K.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

Figures top

	Fig. 1. Perspective view of the cation of the title compound (I), with the atom-numbering scheme; displacement ellipsoids are at the 50% probability level.
	Fig. 2. Perspective view of the anion of the title compound (I), with the atom-numbering scheme; displacement ellipsoids are at the 50% probability level.

Tetra-n-butylammonium tetrakis(pentafluorophenyl)borate top

Crystal data top

C₁₆H₃₆N⁺·C₂₄BF₂₀⁻	F(000) = 1872
M_r = 921.51	D_x = 1.480 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 10062 reflections
a = 24.104 (2) Å	θ = 3.6–25.6°
b = 12.8925 (12) Å	µ = 0.15 mm⁻¹
c = 17.5363 (15) Å	T = 173 K
β = 130.629 (5)°	Plate, colourless
V = 4135.9 (7) Å³	0.42 × 0.37 × 0.21 mm
Z = 4

Data collection top

Stoe IPDS-II two-circle diffractometer	3371 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.035
Graphite monochromator	θ_max = 25.6°, θ_min = 3.6°
ω scans	h = −29→29
10176 measured reflections	k = −15→14
3854 independent reflections	l = −21→17

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.033	H-atom parameters constrained
wR(F²) = 0.075	w = 1/[σ²(F_o²) + (0.0476P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
3854 reflections	Δρ_max = 0.25 e Å⁻³
560 parameters	Δρ_min = −0.19 e Å⁻³
2 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0036 (4)

Crystal data top

C₁₆H₃₆N⁺·C₂₄BF₂₀⁻	V = 4135.9 (7) Å³
M_r = 921.51	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 24.104 (2) Å	µ = 0.15 mm⁻¹
b = 12.8925 (12) Å	T = 173 K
c = 17.5363 (15) Å	0.42 × 0.37 × 0.21 mm
β = 130.629 (5)°

Data collection top

Stoe IPDS-II two-circle diffractometer	3371 reflections with I > 2σ(I)
10176 measured reflections	R_int = 0.035
3854 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	2 restraints
wR(F²) = 0.075	H-atom parameters constrained
S = 1.00	Δρ_max = 0.25 e Å⁻³
3854 reflections	Δρ_min = −0.19 e Å⁻³
560 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.61054 (12)	0.60402 (18)	0.24676 (17)	0.0256 (5)
C11	0.64394 (15)	0.6044 (2)	0.1969 (2)	0.0310 (6)
H11A	0.6733	0.5404	0.2173	0.037*
H11B	0.6036	0.6008	0.1232	0.037*
C12	0.69200 (16)	0.6962 (3)	0.2193 (2)	0.0361 (7)
H12A	0.7320	0.7032	0.2928	0.043*
H12B	0.6628	0.7608	0.1939	0.043*
C13	0.7240 (2)	0.6789 (3)	0.1681 (3)	0.0481 (9)
H13A	0.7525	0.6136	0.1935	0.058*
H13B	0.6835	0.6710	0.0948	0.058*
C14	0.7728 (2)	0.7668 (4)	0.1864 (3)	0.0617 (11)
H14A	0.7917	0.7521	0.1521	0.093*
H14B	0.8137	0.7738	0.2587	0.093*
H14C	0.7446	0.8315	0.1602	0.093*
C21	0.56444 (14)	0.7012 (2)	0.2191 (2)	0.0295 (6)
H21A	0.5962	0.7628	0.2414	0.035*
H21B	0.5469	0.7004	0.2568	0.035*
C22	0.49841 (16)	0.7129 (3)	0.1072 (2)	0.0369 (7)
H22A	0.4619	0.6587	0.0864	0.044*
H22B	0.5140	0.7038	0.0676	0.044*
C23	0.46363 (17)	0.8210 (3)	0.0862 (3)	0.0422 (8)
H23A	0.4489	0.8304	0.1270	0.051*
H23B	0.5001	0.8751	0.1062	0.051*
C24	0.3969 (2)	0.8333 (4)	−0.0249 (3)	0.0704 (13)
H24A	0.3757	0.9024	−0.0365	0.106*
H24B	0.3605	0.7804	−0.0444	0.106*
H24C	0.4116	0.8250	−0.0651	0.106*
C31	0.56402 (14)	0.5057 (2)	0.2091 (2)	0.0304 (6)
H31A	0.5239	0.5124	0.1357	0.036*
H31B	0.5948	0.4465	0.2204	0.036*
C32	0.53067 (15)	0.4794 (2)	0.2558 (2)	0.0338 (7)
H32A	0.5042	0.5404	0.2524	0.041*
H32B	0.5697	0.4607	0.3273	0.041*
C33	0.47727 (17)	0.3875 (3)	0.1987 (3)	0.0430 (8)
H33A	0.4372	0.4082	0.1281	0.052*
H33B	0.5035	0.3286	0.1984	0.052*
C34	0.44466 (19)	0.3520 (3)	0.2450 (3)	0.0514 (9)
H34A	0.4114	0.2937	0.2061	0.077*
H34B	0.4176	0.4095	0.2441	0.077*
H34C	0.4840	0.3300	0.3145	0.077*
C41	0.67008 (14)	0.6039 (2)	0.3612 (2)	0.0289 (6)
H41A	0.6461	0.6031	0.3904	0.035*
H41B	0.6977	0.6697	0.3820	0.035*
C42	0.72461 (15)	0.5140 (2)	0.4067 (2)	0.0352 (7)
H42A	0.6981	0.4473	0.3866	0.042*
H42B	0.7510	0.5155	0.3811	0.042*
C43	0.77918 (19)	0.5229 (3)	0.5212 (3)	0.0533 (10)
H43A	0.8034	0.5915	0.5405	0.064*
H43B	0.7525	0.5186	0.5463	0.064*
C44	0.8373 (2)	0.4380 (4)	0.5708 (3)	0.0707 (13)
H44A	0.8711	0.4470	0.6439	0.106*
H44B	0.8644	0.4426	0.5470	0.106*
H44C	0.8137	0.3700	0.5534	0.106*
B1	0.66892 (15)	0.8245 (2)	0.6377 (2)	0.0267 (7)
C51	0.69289 (14)	0.8611 (2)	0.7464 (2)	0.0307 (6)
C52	0.67714 (15)	0.8076 (2)	0.7994 (2)	0.0318 (7)
C53	0.70806 (16)	0.8299 (3)	0.8975 (2)	0.0395 (8)
C54	0.75644 (17)	0.9112 (3)	0.9473 (2)	0.0450 (9)
C55	0.77308 (16)	0.9691 (3)	0.8986 (3)	0.0456 (9)
C56	0.74230 (15)	0.9430 (2)	0.8013 (2)	0.0355 (7)
F52	0.63068 (9)	0.72564 (14)	0.75808 (13)	0.0382 (4)
F53	0.69128 (11)	0.77175 (18)	0.94440 (15)	0.0530 (5)
F54	0.78745 (12)	0.9329 (2)	1.04277 (16)	0.0678 (7)
F55	0.81979 (12)	1.05024 (18)	0.94517 (18)	0.0671 (7)
F56	0.76299 (9)	0.99921 (15)	0.75826 (15)	0.0470 (5)
C61	0.74742 (13)	0.7703 (2)	0.6779 (2)	0.0265 (6)
C62	0.77319 (14)	0.6790 (2)	0.7340 (2)	0.0290 (6)
C63	0.83933 (16)	0.6326 (2)	0.7764 (2)	0.0360 (7)
C64	0.88533 (15)	0.6792 (3)	0.7655 (3)	0.0389 (8)
C65	0.86395 (16)	0.7705 (3)	0.7136 (3)	0.0393 (8)
C66	0.79684 (15)	0.8148 (2)	0.6713 (2)	0.0340 (7)
F62	0.73175 (9)	0.62986 (13)	0.75040 (13)	0.0367 (4)
F63	0.85944 (11)	0.54327 (16)	0.82907 (17)	0.0560 (6)
F64	0.95076 (10)	0.63638 (18)	0.80680 (17)	0.0598 (6)
F65	0.90943 (10)	0.81897 (19)	0.70413 (19)	0.0612 (6)
F66	0.78207 (10)	0.90545 (15)	0.62323 (17)	0.0523 (5)
C71	0.59821 (14)	0.7430 (2)	0.5742 (2)	0.0295 (6)
C72	0.53329 (15)	0.7732 (3)	0.5523 (2)	0.0354 (7)
C73	0.47022 (15)	0.7150 (3)	0.4972 (2)	0.0419 (8)
C74	0.46859 (16)	0.6204 (3)	0.4592 (2)	0.0486 (10)
C75	0.53079 (17)	0.5859 (3)	0.4778 (2)	0.0404 (8)
C76	0.59300 (15)	0.6479 (2)	0.5325 (2)	0.0303 (6)
F72	0.53057 (9)	0.86540 (16)	0.58706 (15)	0.0465 (5)
F73	0.40965 (9)	0.7483 (2)	0.48013 (16)	0.0627 (7)
F74	0.40851 (11)	0.5594 (2)	0.40697 (16)	0.0744 (8)
F75	0.53156 (12)	0.49197 (17)	0.44367 (16)	0.0597 (6)
F76	0.65056 (9)	0.60800 (13)	0.54421 (14)	0.0388 (4)
C81	0.63873 (14)	0.9184 (2)	0.5543 (2)	0.0278 (6)
C82	0.61177 (14)	1.0149 (2)	0.5527 (2)	0.0320 (7)
C83	0.58003 (15)	1.0861 (2)	0.4744 (3)	0.0379 (8)
C84	0.57319 (16)	1.0626 (2)	0.3925 (2)	0.0378 (8)
C85	0.59861 (16)	0.9677 (3)	0.3893 (2)	0.0350 (7)
C86	0.62890 (14)	0.8988 (2)	0.4680 (2)	0.0307 (6)
F82	0.61493 (9)	1.04563 (15)	0.62939 (14)	0.0421 (5)
F83	0.55578 (11)	1.17893 (15)	0.47944 (16)	0.0543 (6)
F84	0.54181 (11)	1.13036 (16)	0.31562 (15)	0.0533 (5)
F85	0.59221 (11)	0.94263 (16)	0.30900 (14)	0.0493 (5)
F86	0.65015 (10)	0.80543 (13)	0.45761 (14)	0.0395 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0257 (10)	0.0280 (12)	0.0245 (12)	0.0030 (9)	0.0169 (10)	−0.0012 (9)
C11	0.0320 (13)	0.0377 (16)	0.0297 (15)	0.0049 (12)	0.0230 (12)	−0.0015 (13)
C12	0.0378 (15)	0.0408 (18)	0.0337 (16)	−0.0017 (13)	0.0251 (14)	0.0001 (14)
C13	0.0519 (19)	0.053 (2)	0.057 (2)	−0.0025 (16)	0.0433 (18)	0.0000 (18)
C14	0.060 (2)	0.082 (3)	0.057 (2)	−0.018 (2)	0.044 (2)	−0.004 (2)
C21	0.0291 (13)	0.0300 (15)	0.0291 (15)	0.0057 (11)	0.0189 (12)	0.0007 (12)
C22	0.0331 (14)	0.0422 (18)	0.0290 (16)	0.0087 (13)	0.0173 (13)	0.0045 (13)
C23	0.0367 (15)	0.045 (2)	0.0399 (18)	0.0108 (14)	0.0230 (15)	0.0114 (15)
C24	0.059 (2)	0.080 (3)	0.046 (2)	0.032 (2)	0.023 (2)	0.022 (2)
C31	0.0300 (13)	0.0265 (15)	0.0316 (15)	−0.0005 (11)	0.0187 (12)	−0.0039 (12)
C32	0.0305 (13)	0.0348 (17)	0.0358 (16)	−0.0008 (12)	0.0215 (13)	0.0014 (13)
C33	0.0339 (15)	0.047 (2)	0.0465 (19)	−0.0048 (13)	0.0253 (14)	−0.0084 (16)
C34	0.0435 (17)	0.050 (2)	0.064 (2)	−0.0177 (16)	0.0368 (18)	−0.0121 (19)
C41	0.0262 (13)	0.0343 (16)	0.0226 (13)	−0.0002 (11)	0.0143 (11)	−0.0023 (12)
C42	0.0299 (13)	0.0355 (16)	0.0323 (16)	0.0037 (12)	0.0167 (12)	−0.0014 (13)
C43	0.0413 (17)	0.069 (3)	0.0348 (18)	0.0152 (17)	0.0181 (15)	0.0096 (17)
C44	0.049 (2)	0.071 (3)	0.055 (3)	0.016 (2)	0.0180 (19)	0.019 (2)
B1	0.0219 (13)	0.0237 (16)	0.0325 (17)	−0.0010 (11)	0.0168 (13)	0.0010 (13)
C51	0.0252 (12)	0.0284 (15)	0.0334 (15)	0.0027 (11)	0.0168 (12)	−0.0020 (13)
C52	0.0300 (13)	0.0314 (16)	0.0323 (16)	0.0042 (12)	0.0196 (13)	−0.0025 (13)
C53	0.0378 (16)	0.0423 (19)	0.0366 (17)	0.0125 (13)	0.0234 (15)	−0.0006 (14)
C54	0.0442 (17)	0.051 (2)	0.0335 (17)	0.0105 (15)	0.0225 (15)	−0.0113 (16)
C55	0.0319 (15)	0.0325 (17)	0.050 (2)	0.0003 (12)	0.0169 (15)	−0.0172 (15)
C56	0.0297 (13)	0.0274 (16)	0.0416 (18)	0.0017 (12)	0.0198 (13)	−0.0001 (14)
F52	0.0409 (9)	0.0414 (10)	0.0371 (9)	−0.0065 (8)	0.0276 (8)	−0.0020 (8)
F53	0.0601 (11)	0.0694 (15)	0.0405 (11)	0.0124 (10)	0.0377 (10)	0.0064 (10)
F54	0.0681 (13)	0.0817 (17)	0.0405 (12)	0.0040 (12)	0.0295 (11)	−0.0237 (11)
F55	0.0563 (12)	0.0520 (13)	0.0639 (15)	−0.0142 (10)	0.0262 (11)	−0.0311 (11)
F56	0.0350 (9)	0.0360 (10)	0.0538 (12)	−0.0068 (8)	0.0217 (8)	−0.0011 (9)
C61	0.0231 (12)	0.0229 (13)	0.0289 (14)	−0.0024 (10)	0.0149 (11)	−0.0017 (11)
C62	0.0267 (12)	0.0309 (15)	0.0283 (15)	−0.0036 (11)	0.0175 (12)	−0.0010 (12)
C63	0.0351 (14)	0.0303 (16)	0.0296 (15)	0.0056 (13)	0.0153 (13)	0.0021 (13)
C64	0.0243 (13)	0.0443 (19)	0.0391 (17)	0.0092 (13)	0.0166 (13)	−0.0057 (15)
C65	0.0279 (14)	0.0448 (19)	0.0479 (19)	−0.0072 (13)	0.0259 (14)	−0.0073 (16)
C66	0.0288 (13)	0.0313 (16)	0.0428 (17)	0.0005 (12)	0.0237 (13)	0.0035 (14)
F62	0.0403 (9)	0.0310 (9)	0.0413 (10)	−0.0016 (7)	0.0276 (8)	0.0071 (8)
F63	0.0524 (11)	0.0414 (11)	0.0569 (12)	0.0214 (9)	0.0279 (10)	0.0220 (10)
F64	0.0298 (9)	0.0715 (15)	0.0656 (14)	0.0190 (9)	0.0255 (9)	0.0037 (11)
F65	0.0399 (10)	0.0694 (15)	0.0888 (17)	−0.0036 (10)	0.0483 (12)	0.0058 (12)
F66	0.0408 (10)	0.0423 (11)	0.0792 (14)	0.0023 (8)	0.0415 (10)	0.0228 (11)
C71	0.0263 (13)	0.0369 (16)	0.0229 (13)	−0.0053 (12)	0.0150 (11)	0.0025 (12)
C72	0.0283 (13)	0.0485 (19)	0.0282 (15)	0.0022 (13)	0.0179 (12)	0.0087 (14)
C73	0.0223 (13)	0.066 (2)	0.0303 (16)	0.0000 (14)	0.0142 (12)	0.0163 (16)
C74	0.0268 (15)	0.077 (3)	0.0238 (16)	−0.0220 (16)	0.0084 (13)	0.0050 (17)
C75	0.0489 (18)	0.0433 (19)	0.0227 (15)	−0.0170 (14)	0.0205 (14)	−0.0050 (14)
C76	0.0312 (13)	0.0357 (17)	0.0237 (14)	−0.0064 (12)	0.0179 (12)	0.0004 (12)
F72	0.0340 (9)	0.0542 (13)	0.0543 (12)	0.0081 (8)	0.0300 (9)	0.0046 (10)
F73	0.0238 (8)	0.1052 (19)	0.0526 (12)	0.0020 (10)	0.0220 (8)	0.0192 (12)
F74	0.0425 (11)	0.105 (2)	0.0475 (13)	−0.0463 (12)	0.0167 (10)	−0.0137 (13)
F75	0.0745 (14)	0.0550 (13)	0.0430 (11)	−0.0352 (11)	0.0353 (11)	−0.0229 (10)
F76	0.0446 (9)	0.0337 (9)	0.0428 (10)	−0.0068 (8)	0.0305 (8)	−0.0097 (8)
C81	0.0219 (12)	0.0265 (15)	0.0323 (15)	0.0004 (10)	0.0164 (11)	0.0004 (12)
C82	0.0282 (13)	0.0310 (16)	0.0330 (15)	0.0015 (12)	0.0182 (12)	−0.0010 (13)
C83	0.0309 (14)	0.0267 (16)	0.0443 (18)	0.0035 (12)	0.0192 (14)	0.0023 (13)
C84	0.0301 (13)	0.0331 (16)	0.0350 (17)	0.0002 (12)	0.0145 (13)	0.0098 (14)
C85	0.0321 (14)	0.0369 (18)	0.0305 (15)	−0.0049 (12)	0.0179 (12)	0.0005 (13)
C86	0.0295 (13)	0.0254 (15)	0.0337 (15)	−0.0009 (11)	0.0190 (12)	−0.0001 (12)
F82	0.0450 (10)	0.0368 (10)	0.0447 (10)	0.0112 (8)	0.0293 (9)	0.0003 (8)
F83	0.0603 (12)	0.0352 (11)	0.0572 (13)	0.0208 (9)	0.0337 (10)	0.0102 (9)
F84	0.0525 (11)	0.0430 (11)	0.0440 (11)	0.0101 (9)	0.0225 (9)	0.0180 (9)
F85	0.0624 (11)	0.0476 (12)	0.0373 (10)	−0.0012 (9)	0.0321 (9)	0.0044 (9)
F86	0.0536 (10)	0.0292 (9)	0.0442 (10)	0.0040 (8)	0.0356 (9)	0.0006 (8)

Geometric parameters (Å, º) top

N1—C11	1.527 (4)	C44—H44B	0.9800
N1—C31	1.528 (4)	C44—H44C	0.9800
N1—C41	1.529 (3)	B1—C81	1.657 (4)
N1—C21	1.529 (3)	B1—C51	1.660 (5)
C11—C12	1.518 (4)	B1—C71	1.666 (4)
C11—H11A	0.9900	B1—C61	1.681 (4)
C11—H11B	0.9900	C51—C52	1.394 (5)
C12—C13	1.535 (5)	C51—C56	1.403 (4)
C12—H12A	0.9900	C52—F52	1.356 (4)
C12—H12B	0.9900	C52—C53	1.389 (5)
C13—C14	1.509 (5)	C53—F53	1.354 (4)
C13—H13A	0.9900	C53—C54	1.377 (5)
C13—H13B	0.9900	C54—F54	1.345 (4)
C14—H14A	0.9800	C54—C55	1.376 (6)
C14—H14B	0.9800	C55—F55	1.354 (4)
C14—H14C	0.9800	C55—C56	1.388 (5)
C21—C22	1.529 (4)	C56—F56	1.354 (4)
C21—H21A	0.9900	C61—C62	1.393 (4)
C21—H21B	0.9900	C61—C66	1.393 (4)
C22—C23	1.542 (5)	C62—F62	1.363 (3)
C22—H22A	0.9900	C62—C63	1.382 (4)
C22—H22B	0.9900	C63—F63	1.352 (4)
C23—C24	1.526 (5)	C63—C64	1.380 (5)
C23—H23A	0.9900	C64—F64	1.352 (3)
C23—H23B	0.9900	C64—C65	1.368 (5)
C24—H24A	0.9800	C65—F65	1.362 (4)
C24—H24B	0.9800	C65—C66	1.389 (4)
C24—H24C	0.9800	C66—F66	1.347 (4)
C31—C32	1.512 (4)	C71—C76	1.390 (4)
C31—H31A	0.9900	C71—C72	1.402 (4)
C31—H31B	0.9900	C72—F72	1.358 (4)
C32—C33	1.544 (4)	C72—C73	1.376 (4)
C32—H32A	0.9900	C73—F73	1.355 (4)
C32—H32B	0.9900	C73—C74	1.378 (6)
C33—C34	1.522 (5)	C74—F74	1.352 (4)
C33—H33A	0.9900	C74—C75	1.383 (5)
C33—H33B	0.9900	C75—F75	1.357 (4)
C34—H34A	0.9800	C75—C76	1.391 (4)
C34—H34B	0.9800	C76—F76	1.365 (4)
C34—H34C	0.9800	C81—C86	1.394 (5)
C41—C42	1.530 (4)	C81—C82	1.396 (4)
C41—H41A	0.9900	C82—F82	1.356 (4)
C41—H41B	0.9900	C82—C83	1.394 (5)
C42—C43	1.528 (5)	C83—F83	1.359 (4)
C42—H42A	0.9900	C83—C84	1.370 (5)
C42—H42B	0.9900	C84—F84	1.351 (4)
C43—C44	1.526 (5)	C84—C85	1.386 (5)
C43—H43A	0.9900	C85—F85	1.352 (4)
C43—H43B	0.9900	C85—C86	1.383 (4)
C44—H44A	0.9800	C86—F86	1.366 (3)

C11—N1—C31	105.5 (2)	C44—C43—C42	112.4 (3)
C11—N1—C41	111.0 (2)	C44—C43—H43A	109.1
C31—N1—C41	111.3 (2)	C42—C43—H43A	109.1
C11—N1—C21	111.2 (2)	C44—C43—H43B	109.1
C31—N1—C21	111.4 (2)	C42—C43—H43B	109.1
C41—N1—C21	106.5 (2)	H43A—C43—H43B	107.9
C12—C11—N1	116.9 (2)	C43—C44—H44A	109.5
C12—C11—H11A	108.1	C43—C44—H44B	109.5
N1—C11—H11A	108.1	H44A—C44—H44B	109.5
C12—C11—H11B	108.1	C43—C44—H44C	109.5
N1—C11—H11B	108.1	H44A—C44—H44C	109.5
H11A—C11—H11B	107.3	H44B—C44—H44C	109.5
C11—C12—C13	108.9 (3)	C81—B1—C51	115.4 (2)
C11—C12—H12A	109.9	C81—B1—C71	101.6 (2)
C13—C12—H12A	109.9	C51—B1—C71	112.7 (2)
C11—C12—H12B	109.9	C81—B1—C61	113.7 (2)
C13—C12—H12B	109.9	C51—B1—C61	100.4 (2)
H12A—C12—H12B	108.3	C71—B1—C61	113.6 (2)
C14—C13—C12	112.7 (3)	C52—C51—C56	113.1 (3)
C14—C13—H13A	109.1	C52—C51—B1	125.7 (3)
C12—C13—H13A	109.1	C56—C51—B1	120.5 (3)
C14—C13—H13B	109.1	F52—C52—C53	114.4 (3)
C12—C13—H13B	109.1	F52—C52—C51	121.2 (3)
H13A—C13—H13B	107.8	C53—C52—C51	124.4 (3)
C13—C14—H14A	109.5	F53—C53—C54	120.0 (3)
C13—C14—H14B	109.5	F53—C53—C52	120.5 (3)
H14A—C14—H14B	109.5	C54—C53—C52	119.5 (3)
C13—C14—H14C	109.5	F54—C54—C55	120.6 (3)
H14A—C14—H14C	109.5	F54—C54—C53	120.2 (4)
H14B—C14—H14C	109.5	C55—C54—C53	119.2 (3)
N1—C21—C22	115.0 (2)	F55—C55—C54	120.5 (3)
N1—C21—H21A	108.5	F55—C55—C56	119.9 (4)
C22—C21—H21A	108.5	C54—C55—C56	119.6 (3)
N1—C21—H21B	108.5	F56—C56—C55	117.4 (3)
C22—C21—H21B	108.5	F56—C56—C51	118.5 (3)
H21A—C21—H21B	107.5	C55—C56—C51	124.1 (3)
C21—C22—C23	110.2 (3)	C62—C61—C66	113.2 (2)
C21—C22—H22A	109.6	C62—C61—B1	120.7 (2)
C23—C22—H22A	109.6	C66—C61—B1	125.7 (3)
C21—C22—H22B	109.6	F62—C62—C63	115.6 (3)
C23—C22—H22B	109.6	F62—C62—C61	119.4 (2)
H22A—C22—H22B	108.1	C63—C62—C61	125.1 (3)
C24—C23—C22	110.9 (3)	F63—C63—C64	120.1 (3)
C24—C23—H23A	109.5	F63—C63—C62	120.8 (3)
C22—C23—H23A	109.5	C64—C63—C62	119.1 (3)
C24—C23—H23B	109.5	F64—C64—C65	120.7 (3)
C22—C23—H23B	109.5	F64—C64—C63	120.7 (3)
H23A—C23—H23B	108.1	C65—C64—C63	118.6 (3)
C23—C24—H24A	109.5	F65—C65—C64	119.5 (3)
C23—C24—H24B	109.5	F65—C65—C66	119.8 (3)
H24A—C24—H24B	109.5	C64—C65—C66	120.8 (3)
C23—C24—H24C	109.5	F66—C66—C65	115.6 (3)
H24A—C24—H24C	109.5	F66—C66—C61	121.2 (2)
H24B—C24—H24C	109.5	C65—C66—C61	123.2 (3)
C32—C31—N1	116.9 (2)	C76—C71—C72	113.4 (3)
C32—C31—H31A	108.1	C76—C71—B1	127.6 (2)
N1—C31—H31A	108.1	C72—C71—B1	118.8 (3)
C32—C31—H31B	108.1	F72—C72—C73	116.0 (3)
N1—C31—H31B	108.1	F72—C72—C71	119.5 (3)
H31A—C31—H31B	107.3	C73—C72—C71	124.6 (3)
C31—C32—C33	109.6 (3)	F73—C73—C72	121.4 (4)
C31—C32—H32A	109.8	F73—C73—C74	119.1 (3)
C33—C32—H32A	109.8	C72—C73—C74	119.5 (3)
C31—C32—H32B	109.8	F74—C74—C73	121.5 (3)
C33—C32—H32B	109.8	F74—C74—C75	119.4 (4)
H32A—C32—H32B	108.2	C73—C74—C75	119.0 (3)
C34—C33—C32	112.8 (3)	F75—C75—C74	120.4 (3)
C34—C33—H33A	109.0	F75—C75—C76	119.9 (3)
C32—C33—H33A	109.0	C74—C75—C76	119.6 (3)
C34—C33—H33B	109.0	F76—C76—C71	121.2 (2)
C32—C33—H33B	109.0	F76—C76—C75	114.9 (3)
H33A—C33—H33B	107.8	C71—C76—C75	123.9 (3)
C33—C34—H34A	109.5	C86—C81—C82	113.0 (3)
C33—C34—H34B	109.5	C86—C81—B1	119.5 (3)
H34A—C34—H34B	109.5	C82—C81—B1	126.9 (3)
C33—C34—H34C	109.5	F82—C82—C83	115.1 (3)
H34A—C34—H34C	109.5	F82—C82—C81	121.0 (3)
H34B—C34—H34C	109.5	C83—C82—C81	123.8 (3)
N1—C41—C42	116.0 (2)	F83—C83—C84	120.0 (3)
N1—C41—H41A	108.3	F83—C83—C82	120.0 (3)
C42—C41—H41A	108.3	C84—C83—C82	120.1 (3)
N1—C41—H41B	108.3	F84—C84—C83	120.7 (3)
C42—C41—H41B	108.3	F84—C84—C85	120.4 (3)
H41A—C41—H41B	107.4	C83—C84—C85	118.9 (3)
C43—C42—C41	109.9 (3)	F85—C85—C86	120.9 (3)
C43—C42—H42A	109.7	F85—C85—C84	119.9 (3)
C41—C42—H42A	109.7	C86—C85—C84	119.1 (3)
C43—C42—H42B	109.7	F86—C86—C85	115.6 (3)
C41—C42—H42B	109.7	F86—C86—C81	119.4 (3)
H42A—C42—H42B	108.2	C85—C86—C81	125.0 (3)

C31—N1—C11—C12	178.5 (2)	F64—C64—C65—C66	−179.8 (3)
C41—N1—C11—C12	−60.7 (3)	C63—C64—C65—C66	−1.0 (5)
C21—N1—C11—C12	57.6 (3)	F65—C65—C66—F66	−0.3 (5)
N1—C11—C12—C13	176.4 (3)	C64—C65—C66—F66	179.1 (3)
C11—C12—C13—C14	180.0 (3)	F65—C65—C66—C61	−179.8 (3)
C11—N1—C21—C22	62.4 (3)	C64—C65—C66—C61	−0.4 (5)
C31—N1—C21—C22	−55.0 (3)	C62—C61—C66—F66	−177.4 (3)
C41—N1—C21—C22	−176.6 (3)	B1—C61—C66—F66	−5.2 (5)
N1—C21—C22—C23	−170.9 (3)	C62—C61—C66—C65	2.0 (4)
C21—C22—C23—C24	−179.1 (3)	B1—C61—C66—C65	174.3 (3)
C11—N1—C31—C32	173.5 (2)	C81—B1—C71—C76	106.6 (3)
C41—N1—C31—C32	53.0 (3)	C51—B1—C71—C76	−129.3 (3)
C21—N1—C31—C32	−65.7 (3)	C61—B1—C71—C76	−15.9 (4)
N1—C31—C32—C33	172.1 (2)	C81—B1—C71—C72	−68.7 (3)
C31—C32—C33—C34	176.6 (3)	C51—B1—C71—C72	55.4 (3)
C11—N1—C41—C42	−57.6 (3)	C61—B1—C71—C72	168.8 (3)
C31—N1—C41—C42	59.6 (3)	C76—C71—C72—F72	−178.9 (3)
C21—N1—C41—C42	−178.7 (2)	B1—C71—C72—F72	−3.1 (4)
N1—C41—C42—C43	−178.5 (3)	C76—C71—C72—C73	1.5 (4)
C41—C42—C43—C44	−177.3 (3)	B1—C71—C72—C73	177.4 (3)
C81—B1—C51—C52	138.0 (3)	F72—C72—C73—F73	−0.6 (4)
C71—B1—C51—C52	21.9 (4)	C71—C72—C73—F73	179.0 (3)
C61—B1—C51—C52	−99.4 (3)	F72—C72—C73—C74	179.9 (3)
C81—B1—C51—C56	−52.5 (3)	C71—C72—C73—C74	−0.5 (5)
C71—B1—C51—C56	−168.6 (2)	F73—C73—C74—F74	−1.3 (5)
C61—B1—C51—C56	70.2 (3)	C72—C73—C74—F74	178.2 (3)
C56—C51—C52—F52	−179.6 (2)	F73—C73—C74—C75	−179.1 (3)
B1—C51—C52—F52	−9.4 (4)	C72—C73—C74—C75	0.3 (5)
C56—C51—C52—C53	−1.7 (4)	F74—C74—C75—F75	0.4 (5)
B1—C51—C52—C53	168.5 (3)	C73—C74—C75—F75	178.3 (3)
F52—C52—C53—F53	0.1 (4)	F74—C74—C75—C76	−179.2 (3)
C51—C52—C53—F53	−177.9 (3)	C73—C74—C75—C76	−1.3 (5)
F52—C52—C53—C54	179.7 (3)	C72—C71—C76—F76	178.3 (3)
C51—C52—C53—C54	1.6 (4)	B1—C71—C76—F76	2.8 (4)
F53—C53—C54—F54	0.3 (4)	C72—C71—C76—C75	−2.5 (4)
C52—C53—C54—F54	−179.2 (3)	B1—C71—C76—C75	−178.0 (3)
F53—C53—C54—C55	179.7 (3)	F75—C75—C76—F76	2.2 (4)
C52—C53—C54—C55	0.1 (4)	C74—C75—C76—F76	−178.2 (3)
F54—C54—C55—F55	−1.4 (5)	F75—C75—C76—C71	−177.0 (3)
C53—C54—C55—F55	179.2 (3)	C74—C75—C76—C71	2.5 (5)
F54—C54—C55—C56	177.8 (3)	C51—B1—C81—C86	169.4 (2)
C53—C54—C55—C56	−1.5 (5)	C71—B1—C81—C86	−68.4 (3)
F55—C55—C56—F56	2.3 (4)	C61—B1—C81—C86	54.1 (3)
C54—C55—C56—F56	−177.0 (3)	C51—B1—C81—C82	−19.9 (4)
F55—C55—C56—C51	−179.4 (3)	C71—B1—C81—C82	102.4 (3)
C54—C55—C56—C51	1.4 (5)	C61—B1—C81—C82	−135.2 (3)
C52—C51—C56—F56	178.6 (2)	C86—C81—C82—F82	178.2 (2)
B1—C51—C56—F56	7.8 (4)	B1—C81—C82—F82	7.0 (4)
C52—C51—C56—C55	0.2 (4)	C86—C81—C82—C83	−1.7 (4)
B1—C51—C56—C55	−170.5 (3)	B1—C81—C82—C83	−172.9 (3)
C81—B1—C61—C62	−168.6 (2)	F82—C82—C83—F83	0.7 (4)
C51—B1—C61—C62	67.5 (3)	C81—C82—C83—F83	−179.4 (2)
C71—B1—C61—C62	−53.1 (4)	F82—C82—C83—C84	−179.2 (3)
C81—B1—C61—C66	19.7 (4)	C81—C82—C83—C84	0.7 (4)
C51—B1—C61—C66	−104.2 (3)	F83—C83—C84—F84	−0.7 (4)
C71—B1—C61—C66	135.2 (3)	C82—C83—C84—F84	179.2 (3)
C66—C61—C62—F62	177.0 (3)	F83—C83—C84—C85	179.7 (3)
B1—C61—C62—F62	4.4 (4)	C82—C83—C84—C85	−0.4 (4)
C66—C61—C62—C63	−2.5 (4)	F84—C84—C85—F85	0.2 (4)
B1—C61—C62—C63	−175.2 (3)	C83—C84—C85—F85	179.8 (3)
F62—C62—C63—F63	1.0 (4)	F84—C84—C85—C86	−178.5 (3)
C61—C62—C63—F63	−179.5 (3)	C83—C84—C85—C86	1.1 (4)
F62—C62—C63—C64	−178.2 (3)	F85—C85—C86—F86	−1.0 (4)
C61—C62—C63—C64	1.3 (5)	C84—C85—C86—F86	177.6 (2)
F63—C63—C64—F64	0.2 (5)	F85—C85—C86—C81	179.0 (3)
C62—C63—C64—F64	179.4 (3)	C84—C85—C86—C81	−2.4 (4)
F63—C63—C64—C65	−178.7 (3)	C82—C81—C86—F86	−177.5 (2)
C62—C63—C64—C65	0.6 (5)	B1—C81—C86—F86	−5.5 (4)
F64—C64—C65—F65	−0.5 (5)	C82—C81—C86—C85	2.6 (4)
C63—C64—C65—F65	178.4 (3)	B1—C81—C86—C85	174.5 (2)

Experimental details

Crystal data
Chemical formula	C₁₆H₃₆N⁺·C₂₄BF₂₀⁻
M_r	921.51
Crystal system, space group	Monoclinic, Cc
Temperature (K)	173
a, b, c (Å)	24.104 (2), 12.8925 (12), 17.5363 (15)
β (°)	130.629 (5)
V (Å³)	4135.9 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.15
Crystal size (mm)	0.42 × 0.37 × 0.21

Data collection
Diffractometer	Stoe IPDS-II two-circle diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10176, 3854, 3371
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.608

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.075, 1.00
No. of reflections	3854
No. of parameters	560
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.19

Computer programs: X-AREA (Stoe & Cie, 2001), X-AREA, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), XP in SHELXTL-Plus (Sheldrick, 1991), SHELXL97 and PLATON (Spek, 2003).

Selected bond lengths (Å) top

N1—C11	1.527 (4)	B1—C81	1.657 (4)
N1—C31	1.528 (4)	B1—C51	1.660 (5)
N1—C41	1.529 (3)	B1—C71	1.666 (4)
N1—C21	1.529 (3)	B1—C61	1.681 (4)

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